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Compound Detail

CHEMBL489140

KAURENOIC ACID
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C=C1C[C@@]23CC[C@H]4[C@@](C)(CCC[C@@]4(C)C(=O)O)[C@@H]2CC[C@@H]1C3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL489140
Name KAURENOIC ACID
Phase Preclinical
Structure Type MOL
InChI Key NIKHGUQULKYIGE-OTCXFQBHSA-N
11
Targets
20
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

302.5
MW (Da)
5.04
ALogP
1
HBA
1
HBD
37.3
PSA (Ų)
0.69
QED
1
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H30O2
MW 302.46
Aromatic Rings 0
Heavy Atoms 22
NP-Likeness 3.10

Activity Summary

IC50 19 meas. best 8.7
EC50 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
PBMC
CHEMBL613107
 IC50 8.7 6.475 2.0 4
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL3910
 IC50 6.45 6.45 357.0 1
Leishmania amazonensis
CHEMBL612877
 IC50 4.93 4.48 11660.0 2
Trypanosoma cruzi
CHEMBL368
 IC50 4.78 4.78 16500.0 1
Tyrosine-protein phosphatase non-receptor type 1
CHEMBL335
 IC50 4.7 4.7 20200.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.68 4.68 21100.0 1
Dihydroorotate dehydrogenase (fumarate)
CHEMBL4295843
 IC50 4.5 4.5 31500.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.36 4.31 44110.0 2
Unchecked
CHEMBL612545
 IC50 4.3 4.3 50000.0 1
HepG2
CHEMBL395
 IC50 4.29 4.29 50720.0 1
K562
CHEMBL385
 IC50 4.14 4.14 72530.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
PBMC IC50 = 2.0 nM 8.7 Antiinflammatory activity in human PBMC assessed as inhibition of LPS-induced TN... 25338180
PBMC IC50 = 10.0 nM 8.0 Antiinflammatory activity in human PBMC assessed as inhibition of LPS-induced IL... 25338180
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 357.0 nM 6.45 Inhibition of mouse 11beta-HSD1 expressed in HEK293 cell microsomes assessed as ... 23747808
PBMC IC50 = 7700.0 nM 5.11 Antiinflammatory activity in human PBMC assessed as inhibition of LPS-induced IL... 25338180
Leishmania amazonensis IC50 = 11660.0 nM 4.93 Antileishmanial activity against Leishmania amazonensis WHOM/BR/75/Josefa amasti... 30145372
Trypanosoma cruzi IC50 = 16500.0 nM 4.78 Antitrypanosomal activity against Trypanosoma cruzi Y amastigotes infected in mo... 22440015
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 20200.0 nM 4.7 Inhibition of human recombinant PTP1B 16545563
Plasmodium falciparum IC50 = 21100.0 nM 4.68 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 i... 23353738
Dihydroorotate dehydrogenase (fumarate) IC50 = 31500.0 nM 4.5 Inhibition of recombinant oligo-histidine-tagged Leishmania major DHODH expresse... 30145372
Dihydroorotate dehydrogenase (fumarate) IC50 = 31622.78 nM 4.5 Inhibition of recombinant oligo-histidine-tagged Leishmania major DHODH expresse... 30145372
NON-PROTEIN TARGET IC50 = 44110.0 nM 4.36 Cytotoxicity against human HL60 cells after 72 hrs by alamar blue assay 24969014
Unchecked IC50 = 50000.0 nM 4.3 Inhibition of NF-kappaB activation in mouse RaW264.7 cells assessed as reduction... 33306388
HepG2 IC50 = 50720.0 nM 4.29 Cytotoxicity against human HepG2 cells after 72 hrs by alamar blue assay 24969014
NON-PROTEIN TARGET IC50 = 54790.0 nM 4.26 Cytotoxicity against mouse B16F10 cells after 72 hrs by alamar blue assay 24969014
K562 IC50 = 72530.0 nM 4.14 Cytotoxicity against human K562 cells after 72 hrs by alamar blue assay 24969014
PBMC IC50 = 80770.0 nM 4.09 Cytotoxicity against concanavalin-A stimulated human PBMC after 72 hrs by alamar... 24969014
Leishmania amazonensis IC50 = 93260.0 nM 4.03 Antileishmanial activity against Leishmania amazonensis WHOM/BR/75/Josefa promas... 30145372

Literature References

PubMed DOI Target Context # Activities
22574649 10.1021/np200989t Mus musculus 31
22440015 10.1021/jm201451h Trypanosoma cruzi 13
15137820 10.1021/jf030672j Botrytis cinerea 8
33236902 10.1021/acs.jnatprod.0c01050 Schistosoma mansoni 7
17055730 10.1016/j.bmc.2006.09.048 Trypanosoma cruzi 5
12398544 10.1021/np020191e NON-PROTEIN TARGET 4
23747808 10.1016/j.ejmech.2013.05.010 11-beta-hydroxysteroid dehydrogenase 1 4
17055730 10.1016/j.bmc.2006.09.048 Blood 3
23353738 10.1016/j.ejmech.2012.12.010 NON-PROTEIN TARGET 3
25338180 10.1021/np500125x PBMC 3
19548690 10.1021/np9000569 Salmonella enterica subsp. enterica 3
30145372 10.1016/j.ejmech.2018.08.033 Dihydroorotate dehydrogenase (fumarate) 3
19548690 10.1021/np9000569 Mycobacterium tuberculosis 3
21334121 10.1016/j.ejmech.2011.01.052 RAW264.7 2
24969014 10.1016/j.bmcl.2014.06.005 NON-PROTEIN TARGET 2
23747808 10.1016/j.ejmech.2013.05.010 11-beta-hydroxysteroid dehydrogenase type 2 2
22440015 10.1021/jm201451h ADMET 2
33236902 10.1021/acs.jnatprod.0c01050 Unchecked 2
30145372 10.1016/j.ejmech.2018.08.033 Leishmania amazonensis 2
23747808 10.1016/j.ejmech.2013.05.010 Unchecked 2

Data from ChEMBL 36 via Core Engine